Sodium Carbonate → Ethyl 1-{6-[2-(hydroxymethyl)phenyl]pyridin-2-yl}-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255216Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Cl)[N:16]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].B1(O)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH2:24][O:23]1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[OH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:17]1[N:16]=[C:15]([N:9]2[C:10]([C:11]([F:14])([F:13])[F:12])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]2)[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the title compound from Example 1 Step A (300 mg, 0.94 mmol), 2,1-benzoxaborol-1(3H)-ol (189 mg, 1.40 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (94 mg, 0.14 mmol), Na2CO3 (1.4 mL, 2.0 M aqueous, 2.8 mmol) and acetonitrile (1.5 mL) in a nitrogen-filled capped vial was stirred at 100° C. for 1.5 h, cooled, concentrated and purified by silica gel flash chromatography (hexanes-EtOAc, 3:1 to 2:1 v/v) to provide the title compound: LCMS 374.1 [M−OH]+; 1H NMR (400 MHz, CDCl3) δ 8.16 (s, 1H), 8.06 (t, J=7.9 Hz, 1H), 7.77 (d, J=7.6 Hz, 1H), 7.59-7.41 (m, 5H), 4.51 (s, 2H), 4.36 (q, J=7.1 Hz, 2H), 1.40 (t, J=7.1 Hz, 3H).

Workup

additionfilled
customcapped vial
temperaturecooled
concentrationconcentrated
custompurified by silica gel flash chromatography (hexanes-EtOAc, 3:1 to 2:1 v/v)

Sources & evidence

ORD record: ord-f4d8fda6aa6849659cdea09655045c92
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455638B2

Reaction notes

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